JP2008509894A5 - - Google Patents
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- Publication number
- JP2008509894A5 JP2008509894A5 JP2007525218A JP2007525218A JP2008509894A5 JP 2008509894 A5 JP2008509894 A5 JP 2008509894A5 JP 2007525218 A JP2007525218 A JP 2007525218A JP 2007525218 A JP2007525218 A JP 2007525218A JP 2008509894 A5 JP2008509894 A5 JP 2008509894A5
- Authority
- JP
- Japan
- Prior art keywords
- medicament
- formula
- compound
- prevention
- manufacture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 230000004129 fatty acid metabolism Effects 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- -1 sulfonic acid monohydrate Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VNJOEUSYAMPBAK-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrate Chemical compound O.CC1=CC=CC=C1S(O)(=O)=O VNJOEUSYAMPBAK-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)(C(O*)=O)OCC1CC(COCc2c(*)[o]c(-c3ccc(*)c(C)c3*)n2)CCC1 Chemical compound CC(*)(C(O*)=O)OCC1CC(COCc2c(*)[o]c(-c3ccc(*)c(C)c3*)n2)CCC1 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- CPGISPNRQJPVBR-QWHCGFSZSA-N tert-butyl 2-[[(1r,3s)-3-(hydroxymethyl)cyclohexyl]methoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC[C@@H]1CCC[C@H](CO)C1 CPGISPNRQJPVBR-QWHCGFSZSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004039533A DE102004039533B4 (de) | 2004-08-14 | 2004-08-14 | Essigsäurederivate mit Cyclohexylmethoxy-Substituenten, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| PCT/EP2005/008284 WO2006018118A1 (de) | 2004-08-14 | 2005-07-30 | 2-{-3-`2-(phenyl)-oxazol-4-ylmethoxymethyl!-cyclohexylmethoxy}-propionsäure derivate als ppar-liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008509894A JP2008509894A (ja) | 2008-04-03 |
| JP2008509894A5 true JP2008509894A5 (https=) | 2008-09-18 |
Family
ID=35376939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007525218A Abandoned JP2008509894A (ja) | 2004-08-14 | 2005-07-30 | 高脂血症及び糖尿病の治療のためのｐｐａｒリガンド（ペルオキシソーム増殖剤応答性受容体）として使用される２−｛３−［２−（フェニル）−オキサゾール−４−イルメトキシメチル］−シクロヘキシルメトキシ｝−プロピオン酸誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7538131B2 (https=) |
| EP (1) | EP1789402B1 (https=) |
| JP (1) | JP2008509894A (https=) |
| KR (1) | KR20070046116A (https=) |
| CN (1) | CN101014579A (https=) |
| AR (1) | AR050121A1 (https=) |
| AT (1) | ATE449086T1 (https=) |
| AU (1) | AU2005274495A1 (https=) |
| BR (1) | BRPI0514360A (https=) |
| CA (1) | CA2576584A1 (https=) |
| DE (2) | DE102004039533B4 (https=) |
| DK (1) | DK1789402T3 (https=) |
| ES (1) | ES2335513T3 (https=) |
| IL (1) | IL181011A0 (https=) |
| MX (1) | MX2007000846A (https=) |
| PA (1) | PA8641601A1 (https=) |
| PE (1) | PE20060643A1 (https=) |
| PT (1) | PT1789402E (https=) |
| TW (1) | TW200621733A (https=) |
| UY (1) | UY29064A1 (https=) |
| WO (1) | WO2006018118A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009509988A (ja) | 2005-09-29 | 2009-03-12 | サノフィ−アベンティス | フェニル−及びピリジニル−１，２，４−オキサジアゾロン誘導体、その製造方法、及び医薬品としてのその使用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20040199A2 (en) * | 2001-08-31 | 2005-04-30 | Aventis Pharma Deutschland Gmbh | Diaryl cycloalkyl derivatives, method for producing the same and the use thereof as ppar activators |
| DE10308355A1 (de) * | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
-
2004
- 2004-08-14 DE DE102004039533A patent/DE102004039533B4/de not_active Expired - Fee Related
-
2005
- 2005-07-30 KR KR1020077003579A patent/KR20070046116A/ko not_active Withdrawn
- 2005-07-30 DK DK05772372.8T patent/DK1789402T3/da active
- 2005-07-30 BR BRPI0514360-8A patent/BRPI0514360A/pt not_active IP Right Cessation
- 2005-07-30 AT AT05772372T patent/ATE449086T1/de not_active IP Right Cessation
- 2005-07-30 EP EP05772372A patent/EP1789402B1/de not_active Expired - Lifetime
- 2005-07-30 AU AU2005274495A patent/AU2005274495A1/en not_active Abandoned
- 2005-07-30 PT PT05772372T patent/PT1789402E/pt unknown
- 2005-07-30 ES ES05772372T patent/ES2335513T3/es not_active Expired - Lifetime
- 2005-07-30 CN CNA2005800271483A patent/CN101014579A/zh active Pending
- 2005-07-30 MX MX2007000846A patent/MX2007000846A/es active IP Right Grant
- 2005-07-30 CA CA002576584A patent/CA2576584A1/en not_active Abandoned
- 2005-07-30 DE DE502005008552T patent/DE502005008552D1/de not_active Expired - Lifetime
- 2005-07-30 WO PCT/EP2005/008284 patent/WO2006018118A1/de not_active Ceased
- 2005-07-30 JP JP2007525218A patent/JP2008509894A/ja not_active Abandoned
- 2005-08-10 PE PE2005000925A patent/PE20060643A1/es not_active Application Discontinuation
- 2005-08-11 TW TW094127241A patent/TW200621733A/zh unknown
- 2005-08-11 AR ARP050103350A patent/AR050121A1/es not_active Application Discontinuation
- 2005-08-12 PA PA20058641601A patent/PA8641601A1/es unknown
- 2005-08-12 UY UY29064A patent/UY29064A1/es unknown
-
2007
- 2007-01-28 IL IL181011A patent/IL181011A0/en unknown
- 2007-02-02 US US11/670,594 patent/US7538131B2/en not_active Expired - Fee Related
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